Abstract

This study reports the synthesis of some new bicyclic and tricyclic heterocyclic macromolecules incorporated pyrano[3,2-c]pyridine, 1,6-naphthyridine, and pyrimidonaphthyridine rings starting from new dienones, N-benzyl-3,5-bis(arylidene)-piperidin-4-ones. The chemistry involved the cyclocondensation of dienones with malononitrile in the presence of piperidine yielded the target 2-aminopyranopyridine-3-carbonitriles. The reaction of dienones with malononitrile or ethyl cyanoacetate in the presence of excess ammonium acetate afforded the corresponding 2-aminonaphthyridines and/or 2-oxonaphthyridine derivatives, respectively, in good yields. The 2,4-disubstituted pyrimido[4,5-b][1,6]naphthyridines were successfully achieved from the reaction of the 2-aminonaphthyridine derivatives with the appropriate reagents. The structures of the isolated products were determined by elemental analysis and spectral methods (FT-IR, ¹H-NMR, and ¹³C-NMR). The cytotoxicity of some of the prepared derivatives was also investigated.

摘要

本研究报道了一些新的双环和三环杂环大分子的合成，这些大分子包含吡喃并[3,2 - c ]吡啶、1,6-萘啶和嘧啶萘啶环，从新的二烯酮、N -benzyl -3,5-bis(arylidene) -哌啶-4-ones。该化学反应涉及二酮与丙二腈在哌啶存在下的环缩合反应，得到目标 2-氨基吡喃吡啶-3-甲腈。在过量乙酸铵存在下二酮与丙二腈或氰基乙酸乙酯的反应分别以良好的收率得到相应的2-氨基萘啶和/或2-氧代萘啶衍生物。2,4-二取代嘧啶并[4,5- b][1,6]萘啶由 2-氨基萘啶衍生物与适当试剂反应成功制得。分离产物的结构通过元素分析和光谱方法（FT-IR、¹ H-NMR 和¹³ C-NMR）确定。还研究了一些制备的衍生物的细胞毒性。